If you want to be close to all the action in Key West, Florida, but have a calm place to retreat to with a real sense of place, then Winslow’s Bungalows right off Truman Avenue is a great choice. This property was formerly known as Chelsea House and now a Kimpton, part of the IHG group. It’s a few blocks from the lighthouse and Hemingway home, but in a shady, quiet spot where you can kick back by the pool and recharge.
It was formerly part of the Historic Key West Inns collection. These inns are generally not a single home, but rather collections that have been converted from single family houses to different rooms in various configurations. So the Kimpton Winslow’s Bungalows certainly doesn’t come off as a chain hotel. It is a rambling series of buildings straddling a side street, with multiple houses of varying sizes and two swimming pool areas.
This configuration makes the inn feel quite spacious, with off-street parking (a valuable amenity in the historic district), multiple sitting areas, lounge chairs, and hammocks. Most of the rooms have some kind of outdoor sitting area in the form of porch chairs and if not, they’re right by some kind of outdoor living room. 
Naturally the rooms are going to vary quite a bit depending on which house you are in and which part of that house even. That’s part of the charm of an inn like this: no cookie-cutter aesthetic where everything was built to be uniform. There are five general room classes, the smallest having a queen bed and limited space, the largest being a junior suite with a king bed, indoor and outdoor sitting areas, and a kitchenette.
All have very comfortable beds with quality linens, TVs, good WiFi, safes, crisp air-con, and attractive bathrooms with some toiletries included. Although this is a historic inn, the furnishings and design are far from frumpy. There are a few original elements, like the wooden shutters and paneled ceilings, but for the most part you can expect stylish, modern design that won’t feel dated.
This is a full-service hotel, so maids spin through each day and there’s a front desk staffer in the main building that can help with information on setting up tours. Staffers here are friendly and helpful, with lots of local tips on where to eat and what to do. Despite its location close to lots of attractions, our room one house back from Truman Avenue was impressively quiet at night.
A continental breakfast is included in the rates and it’s a good one. There are fresh-baked muffins, bagels, fruit, hard-boiled eggs, and lots more served in an attractive spot by one of the swimming pools. There are no other facilities on site, but dozens of restaurants and bars are just a few blocks away and you can get to Mallory Square by foot in about 15 minutes.
This historic inn has in the past attracted an eclectic clientele of international travelers, a very different crowd than you’ll see pouring out of the cruise ships and heading to Duval Street. At one point we overheard Italian, French, and British English just at breakfast. This is an inn for travelers who want to get a sense of where they are and staying here makes you feel like you’ve got old Key West around you.
Rates start at $179 double for a weekday low season room and will be much higher for weekends in the winter, when northerners are escaping the cold. Alas, unfortunately the corporate overlords at IHG raised the rated by $30 per night by adding an “activity fee” to cover things Chelsea House used to include in the rates because…they’re hotel amenities. Like the breakfast and the WiFi and the bikes you can borrow. Sigh…
Get more information at the official website or book online at Expedia.
